
Episode #120: Dennis Maggard on Solo Sailing
This week’s host John Arndt is joined by Dennis Maggard to chat sailing with me, myself, and I. Dennis has nearly 50,000 miles of sailing under his belt — most of them solo.
Hear about the allure of being alone at sea and disconnecting from life on land, his journey from a Silicon Valley tech employee to spending weeks singlehanding, how to get over seasickness, the sailing legends he’s met along his journey, and his advice on trusting the opportunity sailing presents.
This episode covers everything from Apple to unplugging. Here’s a small sample of what you will hear:
- When did Dennis start sailing?
- What’s his longest singlehanded passage?
- How do you entertain yourself when sailing alone?
- Was the Baja Ha-Ha Dennis’s first big trip?
- How many people do the Baja Ha-Ha?
- Where did Dennis work in the tech world?
- How has sailing changed since he started?
- Short Tacks: What advice does he have for solo sailors?
Learn more about Dennis on Amazon and YouTube.
Listen to the episode on Apple Podcasts, Spotify, and your other favorite podcast spots — follow and leave a 5-star review if you’re feeling the Good Jibes!


Check out the episode and show notes below for much more detail.
Show Notes
- Dennis Maggard on Solo Sailing
- [0:22] Welcome to Good Jibes with Latitude 38
- [0:25] John Arndt
- [0:38] Subscribe to Latitude 38 at Latitude38.com
- [0:51] Learn more about Dennis on Amazon and YouTube
- [1:21] Dove by Robin Lee Graham
- [2:41] How many miles has Dennis sailed?
- [3:08] What’s a story that shaped him as a sailor?
- [4:10] When did he start sailing?
- [5:54] Singlehanded Transpacific Yacht Race (SHTP)
- [7:28] What’s Dennis’s longest singlehanded passage?
- [8:32] How do you entertain yourself when sailing alone?
- [9:30] Where did Dennis work in the tech (technology) world?
- [9:37] Apple, Oracle
- [10:15] How was Dennis’s transition back to sailing?
- [10:52] Apple Card
- [11:44] Larry Ellison
- [14:01] How did Dennis choose his boat?
- [14:14] Latitude 38
- [17:19] Check out the Latitude 38 Classy Classifieds at Latitude38.com/Adverts
- Solo Sailing
- [18:18] Was the Baja Ha-Ha Dennis’s first big trip?
- [19:10] How many people do the Baja Ha-Ha?
- [20:42] What sailing did Dennis do before the Baja Ha-Ha?
- [21:41] How did his wife get into sailing?
- [24:28] Seasickness
- [25:19] Anxiety
- [26:51] What famous sailors has Dennis met?
- [27:33] Episode #23: A Chat with Dustin Reynolds
- [29:41] Episode #115: Ronnie Simpson on Sailing Around the World
- [32:08] Bernard Moitessier
- [34:18] Joshua Slocum
- [35:02] Puget Sound
- [35:50] Channel Islands
- [36:04] Farallones
- [37:38] How has sailing changed since Dennis started?
- [37:42] Starlink
- [41:02] How do you see squall lines?
- [44:22] You can find your closest Latitude 38 distributor at Latitude38.com/Distribution. Did you know every month you can get your copy of Latitude 38 delivered directly to your mailbox? Subscribe at Latitude38.com/Subscriptions
- Short Tacks
- [45:25] What is Dennis’s favorite sailboat?
- [45:51] What’s his racer-cruiser ratio?
- [47:12] What’s his longest passage?
- [49:27] Where hasn’t he sailed but wants to?
- [51:22] What advice does he have for solo sailors?
- [52:49] Does he use a PFD (Personal Flotation Device)?
- [54:15] What’s his biggest fear on the water?
- [56:10] A Voyage for Madmen by Peter Nichols, Sailing Alone Around the World by Joshua Slocum, The Incredible Voyage by Tristan Jones
- [58:02] Check out the Latitude 38 Bookstore here for books recommended by Good Jibes guests
- [59:17] What final thoughts does Dennis have?
- [59:38] Learn more about Dennis on Amazon and YouTube
- [1:00:41] What’s his next trip?
- [1:01:10] Make sure to follow Good Jibes with Latitude 38 on your favorite podcast spot and leave us a 5-star review on Apple Podcasts
- [1:01:12] Got a great sailing story to submit? Do so at [email protected]
- [1:01:15] Subscribe to Latitude 38 at Latitude38.com
- [1:01:16] Email [email protected] to advertise on this podcast or in Latitude 38 sailing magazine
- [1:01:20] Check out the December 2023 issue of Latitude 38
- Theme Song: Pineapple Dream by SOLXIS
Thanks for listening to Dennis Maggard & John Arndt on Good Jibes with Latitude 38. Subscribe here to receive Latitude 38 at your home every month.
What is Good Jibes with Latitude 38?
Welcome to the world of sailing through the eyes of the West Coast Sailor. Each week, hear stories and tips from West Coast sailors on the topics of community, cruising, and racing. Cast off, laugh and learn, and become a better sailor. Hosted by John Arndt, Nicki Bennett, Ryan Foland, and the team at Latitude 38 — the sailing magazine for West Coast sailors since 1977!